EP2423290A4 - PROCESS FOR PREPARING 1-MENTHYL- (3S-) 3-HYDROXYBUTANOATE AND COMPOSITION FOR STIMULATING THE SENSES - Google Patents

PROCESS FOR PREPARING 1-MENTHYL- (3S-) 3-HYDROXYBUTANOATE AND COMPOSITION FOR STIMULATING THE SENSES

Info

Publication number: EP2423290A4
Authority: EP; European Patent Office
Prior art keywords: hydroxybutanoate; menthyl; stimulating; senses; preparing
Prior art date: 2009-04-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

EP10767165.3A

Other languages

German (de)

French (fr)

Other versions

EP2423290A1 (en

EP2423290B1 (en

Inventor

Kazuma Hojo

Takashi Aida

Kenya Ishida

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takasago International Corp

Original Assignee

Takasago International Corp

Takasago Perfumery Industry Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2009-04-24

Filing date

2010-04-23

Publication date

2015-05-27

2010-04-23 Application filed by Takasago International Corp, Takasago Perfumery Industry Co filed Critical Takasago International Corp

2012-02-29 Publication of EP2423290A1 publication Critical patent/EP2423290A1/en

2015-05-27 Publication of EP2423290A4 publication Critical patent/EP2423290A4/en

2019-05-22 Application granted granted Critical

2019-05-22 Publication of EP2423290B1 publication Critical patent/EP2423290B1/en

Status Active legal-status Critical Current

2030-04-23 Anticipated expiration legal-status Critical

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/203—Alicyclic compounds
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/88—Taste or flavour enhancing agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/24—Thermal properties
- A61K2800/244—Endothermic; Cooling; Cooling sensation
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Nutrition Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Birds (AREA)
Emergency Medicine (AREA)
Epidemiology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Oral & Maxillofacial Surgery (AREA)
Wood Science & Technology (AREA)
Inorganic Chemistry (AREA)
Dermatology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Materials Engineering (AREA)
Cosmetics (AREA)
Fats And Perfumes (AREA)
Seasonings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

EP10767165.3A 2009-04-24 2010-04-23 Composition comprising 1-menthyl (3s)-3-hydroxybutanoate for stimulating sense Active EP2423290B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2009106604A JP5546788B2 (en)	2009-04-24	2009-04-24	(3S) -3-Hydroxybutanoic acid-l-menthyl production method and cooling agent composition
PCT/JP2010/057266 WO2010123110A1 (en)	2009-04-24	2010-04-23	Process for producing 1-menthyl (3s)-3-hydroxybutanoate and composition for stimulating sense

Publications (3)

Publication Number	Publication Date
EP2423290A1 EP2423290A1 (en)	2012-02-29
EP2423290A4 true EP2423290A4 (en)	2015-05-27
EP2423290B1 EP2423290B1 (en)	2019-05-22

Family

ID=43011224

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP10767165.3A Active EP2423290B1 (en)	2009-04-24	2010-04-23	Composition comprising 1-menthyl (3s)-3-hydroxybutanoate for stimulating sense

Country Status (9)

Country	Link
US (3)	US8309062B2 (en)
EP (1)	EP2423290B1 (en)
JP (1)	JP5546788B2 (en)
KR (1)	KR20120003462A (en)
CN (1)	CN102414291B (en)
BR (1)	BRPI1015101B1 (en)
MX (2)	MX2011011244A (en)
SG (2)	SG10201401711SA (en)
WO (1)	WO2010123110A1 (en)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20110281945A1 (en) *	2009-01-27	2011-11-17	Yuichi Suzuki	Gastric acid secretion inhibitor, and potassium channel inhibitor
JP5803047B2 (en) *	2011-06-30	2015-11-04	高砂香料工業株式会社	Antibacterial composition
JP2013195289A (en)	2012-03-21	2013-09-30	Takasago Internatl Corp	Method for evaluating sense stimulating component
CN104684412B (en) *	2012-10-05	2017-09-01	小川香料株式会社	Powdered coolant compositions
JP2016102076A (en) *	2014-11-27	2016-06-02	ライオン株式会社	Oral composition
EP3261725B1 (en) *	2015-02-24	2021-10-27	Takasago International Corporation	Enhanced perfume compositions
WO2016197000A1 (en) *	2015-06-04	2016-12-08	P2 Science, Inc.	Olfactive compositions comprising cyclohexyl-alkyl carbinols
JP6391179B2 (en) *	2016-04-01	2018-09-19	長谷川香料株式会社	Emulsified composition and powder composition
WO2018028770A1 (en) *	2016-08-09	2018-02-15	Symrise Ag	Mixtures containing (e)-3-benzo[1,3]dioxol-5-yl-n,n-diphenyl-2-propenamide
KR102493173B1 (en)	2017-01-10	2023-01-27	다카사고 고료 고교 가부시키가이샤	Methyl menthol derivative and cooling agent composition containing the same
US11344488B2 (en)	2017-10-16	2022-05-31	Takasago International Corporation	Cool-sensation imparter composition containing 2,2,6-trimethylcyclohexanecarboxylic acid derivative
WO2020150683A1 (en) *	2019-01-17	2020-07-23	Takasago International Corporation (Usa)	Use of cooling materials for the reduction or inhibition of saltiness in orally administered, imbibed or ingested consumer products
JP7313243B2 (en) *	2019-09-18	2023-07-24	ライオン株式会社	Powder deodorant composition for shoes, containerized powder deodorant composition, and deodorizing method
GB2590973B (en) *	2020-01-10	2022-01-12	Diet Shield Ltd	Composition comprising a lip interacting component
JP7532790B2 (en)	2020-02-07	2024-08-14	三菱瓦斯化学株式会社	Cooling agent composition

Citations (9)

* Cited by examiner, † Cited by third party
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DE2608226A1 (en) *	1976-02-28	1977-09-08	Haarmann & Reimer Gmbh	AGENTS WITH PHYSIOLOGICAL COOLING EFFECT
FR2577922A1 (en) *	1985-02-22	1986-08-29	Takasago Perfumery Co Ltd	L-Menthyl 3-hydroxybutyrate, process for its preparation and cooling agent containing it
EP1176135A1 (en) *	2000-07-25	2002-01-30	Takasago International Corporation	Process for producing optically active alcohol
US20020198412A1 (en) *	2000-02-28	2002-12-26	Green Carter B.	(1R, 2S, 5R)-3-1-menthoxyalkan-1-OL cooling sensate
WO2005049545A1 (en) *	2003-10-31	2005-06-02	Lonza Ag	Process for the preparation of (s)- or (r)-4-halo-3-hydroxybutyrates
US20060269500A1 (en) *	2005-05-31	2006-11-30	Takasago International Corp. (Usa)	Topical warming composition
WO2006137556A1 (en) *	2005-06-21	2006-12-28	Takasago International Corporation	Flavor and fragrance composition
US20080175800A1 (en) *	2007-01-04	2008-07-24	Symrise Gmbh & Co. Kg	Use of specific menthyl 3-oxocarboxylic acid esters as physiologically active cooling substances
EP2423291A1 (en) *	2009-04-24	2012-02-29	Takasago International Corporation	1-menthyl (3r)-3-hydroxybutanoate, process for producing same, and composition containing same for stimulating sense

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JPS4833069A (en)	1971-08-27	1973-05-07
JPS5888334A (en) *	1981-11-20	1983-05-26	Takasago Corp	3-l-menthoxypropane-1,2-diol
JPH02290827A (en)	1989-05-01	1990-11-30	Kao Corp	1-alkoxy-3-l-menthoxypropane-2-ol, cooling agent and cooling composition containing the same compound
JPH05255186A (en) *	1992-03-09	1993-10-05	Hisamitsu Pharmaceut Co Inc	3-substituted-p-menthane derivative and cold-sensation agent containing the same derivative
JP3245748B2 (en)	1992-03-09	2002-01-15	久光製薬株式会社	P-menthane derivative and cooling sensate containing the same
JPH0665023A (en)	1992-08-12	1994-03-08	Hisamitsu Pharmaceut Co Inc	Frigid agent and frigid composition composed of @(3754/24)-)-isopulegol
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2009
- 2009-04-24 JP JP2009106604A patent/JP5546788B2/en active Active
2010
- 2010-04-23 WO PCT/JP2010/057266 patent/WO2010123110A1/en active Application Filing
- 2010-04-23 MX MX2011011244A patent/MX2011011244A/en active IP Right Grant
- 2010-04-23 SG SG10201401711SA patent/SG10201401711SA/en unknown
- 2010-04-23 MX MX2013012386A patent/MX367581B/en unknown
- 2010-04-23 BR BRPI1015101A patent/BRPI1015101B1/en active IP Right Grant
- 2010-04-23 KR KR1020117025140A patent/KR20120003462A/en not_active Application Discontinuation
- 2010-04-23 US US12/766,037 patent/US8309062B2/en active Active
- 2010-04-23 SG SG2011077708A patent/SG175326A1/en unknown
- 2010-04-23 CN CN201080018211.8A patent/CN102414291B/en active Active
- 2010-04-23 EP EP10767165.3A patent/EP2423290B1/en active Active
2012
- 2012-08-31 US US13/601,434 patent/US8586009B2/en active Active
2013
- 2013-10-11 US US14/052,068 patent/US8986660B2/en active Active

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2608226A1 (en) *	1976-02-28	1977-09-08	Haarmann & Reimer Gmbh	AGENTS WITH PHYSIOLOGICAL COOLING EFFECT
FR2577922A1 (en) *	1985-02-22	1986-08-29	Takasago Perfumery Co Ltd	L-Menthyl 3-hydroxybutyrate, process for its preparation and cooling agent containing it
US20020198412A1 (en) *	2000-02-28	2002-12-26	Green Carter B.	(1R, 2S, 5R)-3-1-menthoxyalkan-1-OL cooling sensate
EP1176135A1 (en) *	2000-07-25	2002-01-30	Takasago International Corporation	Process for producing optically active alcohol
WO2005049545A1 (en) *	2003-10-31	2005-06-02	Lonza Ag	Process for the preparation of (s)- or (r)-4-halo-3-hydroxybutyrates
US20060269500A1 (en) *	2005-05-31	2006-11-30	Takasago International Corp. (Usa)	Topical warming composition
WO2006137556A1 (en) *	2005-06-21	2006-12-28	Takasago International Corporation	Flavor and fragrance composition
US20080175800A1 (en) *	2007-01-04	2008-07-24	Symrise Gmbh & Co. Kg	Use of specific menthyl 3-oxocarboxylic acid esters as physiologically active cooling substances
EP2423291A1 (en) *	2009-04-24	2012-02-29	Takasago International Corporation	1-menthyl (3r)-3-hydroxybutanoate, process for producing same, and composition containing same for stimulating sense

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2010123110A1 *

Also Published As

Publication number	Publication date
US20100303740A1 (en)	2010-12-02
BRPI1015101B1 (en)	2019-01-02
EP2423290A1 (en)	2012-02-29
US8309062B2 (en)	2012-11-13
US8586009B2 (en)	2013-11-19
JP2010254621A (en)	2010-11-11
WO2010123110A1 (en)	2010-10-28
MX367581B (en)	2019-08-26
SG10201401711SA (en)	2014-07-30
MX2011011244A (en)	2011-11-07
BRPI1015101A2 (en)	2016-04-26
JP5546788B2 (en)	2014-07-09
CN102414291B (en)	2014-09-03
EP2423290B1 (en)	2019-05-22
SG175326A1 (en)	2011-12-29
US8986660B2 (en)	2015-03-24
KR20120003462A (en)	2012-01-10
CN102414291A (en)	2012-04-11
US20120321773A1 (en)	2012-12-20
US20140037559A1 (en)	2014-02-06

Publication	Publication Date	Title
EP2423290A4 (en)	2015-05-27	PROCESS FOR PREPARING 1-MENTHYL- (3S-) 3-HYDROXYBUTANOATE AND COMPOSITION FOR STIMULATING THE SENSES
EP2423291A4 (en)	2012-09-26	1-MENTHYL- (3R-) 3-HYDROXYBUTANOATE, METHOD FOR THE PRODUCTION THEREOF AND COMPOSITION THEREFOR TO STIMULATE THE SENSES
EP2366794A4 (en)	2015-01-21	PROCESS FOR PREPARING POLY-3-HYDROXYALKANOATE AND POLY-3-HYDROXYALKANOATAGGLOMERATE
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Legal Events

Date	Code	Title	Description
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